Question

Propose a plausible synthesis for the following transformation. OH OH OH 1 = HBr 2 = HBr, HOOH 3 = Br2 4 = Br2, H2O 5 = Br2, CH3OH 6 = TsCl, pyridine 7 = 1) Hg(OAc)2, H2O 2) NaBH4 8 = 1) Hg(OAc)2, EtOH 2) NaBH4 9 = 1) BH3.THF 2) H2O2, NaOH 10 = H2/Pt 11 = 1) MCPBA 2) H+ (aq) 12 = OsO4 (catalytic), NMO 13 = 1) O3 2) DMS 14 = NaOMe 15 = t-BuOK, t-BuOH 16 = 1) xs NaNH2/NH3 2) H2O 14, 2, 15, 12 6, 14, 1, 15, 11 14, 2, 15, 11 6, 14, 2, 15, 12 6, 14, 2, 15, 11

          Propose a plausible synthesis for the following transformation.
OH
OH
OH
1 = HBr
2 = HBr, HOOH
3 = Br2
4 = Br2, H2O
5 = Br2, CH3OH
6 = TsCl, pyridine
7 = 1) Hg(OAc)2, H2O 2) NaBH4
8 = 1) Hg(OAc)2, EtOH 2) NaBH4
9 = 1) BH3.THF 2) H2O2, NaOH
10 = H2/Pt
11 = 1) MCPBA 2) H+ (aq)
12 = OsO4 (catalytic), NMO
13 = 1) O3 2) DMS
14 = NaOMe
15 = t-BuOK, t-BuOH
16 = 1) xs NaNH2/NH3 2) H2O
14, 2, 15, 12
6, 14, 1, 15, 11
14, 2, 15, 11
6, 14, 2, 15, 12
6, 14, 2, 15, 11

Propose a plausible synthesis for the following transformation.
OH
OH
OH
1 = HBr
2 = HBr, HOOH
3 = Br2
4 = Br2, H2O
5 = Br2, CH3OH
6 = TsCl, pyridine
7 = 1) Hg(OAc)2, H2O 2) NaBH4
8 = 1) Hg(OAc)2, EtOH 2) NaBH4
9 = 1) BH3.THF 2) H2O2, NaOH
10 = H2/Pt
11 = 1) MCPBA 2) H+ (aq)
12 = OsO4 (catalytic), NMO
13 = 1) O3 2) DMS
14 = NaOMe
15 = t-BuOK, t-BuOH
16 = 1) xs NaNH2/NH3 2) H2O
14, 2, 15, 12
6, 14, 1, 15, 11
14, 2, 15, 11
6, 14, 2, 15, 12
6, 14, 2, 15, 11

Added by Jose Ignacio V.

Chemistry: Structure and Properties

Nivaldo Tro 2nd Edition

Instant Answer

Solved by Expert Supreeta N

09/09/2023

Step 1

First, we need to protect the alcohol group to avoid any side reactions. We can use TsCl and pyridine for this purpose (step 6). Show more…

Show all steps

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Propose a plausible synthesis for the following transformation: 1 = HBr 2 = HBr, HOOH 3 = Br2 4 = Br2, H2O 5 = Br2, CH3OH 6 = TsCl, pyridine 7 = 1) Hg(OAc)2, H2O 2) NaBH4 8 = 1) Hg(OAc)2, EtOH 2) NaBH4 9 = 1) BH3.THF 2) H2O2, NaOH 10 = H2/Pt 11 = 1) MCPBA 2) H+(aq) 12 = OsO4 (catalytic), NMO 13 = 1) O3 2) DMS 14 = NaOMe 15 = t-BuOK, t-BuOH 16 = 1) xs NaNH2/NH3 2) H2O 14, 2, 15, 12 6, 14, 1, 15, 11 14, 2, 15, 11 6, 14, 2, 15, 12 6, 14, 2, 15, 11